But You Never Know With Whom
by destinedflames
Summary: Elena just moved to NY and now is searching for a good job. Damon is now searching for a good secretary. What if the accidentally meet each other and fall in love? And what about all the bad guys Damon has owed and his ex girlfriend Katherine who really wants to get her toy back? Elena definitely is going to get into trouble... a lot.
1. Chapter 1 Welcome to NY

_First of all, I'd like to thank you for starting to read this fanfic, I've never written any AH AU fanfics, seriously, and I'm not really sure if I'll finish this one, I don't know if you like it or not. So please, review to give me advise and fave/follow if you like it :) If you didn't understand something, just ask in your review. Enjoy! _

**Chapter 1. "Welcome to NY"**

**NY. **

New York is lovely at the end of August. People are coming back from their vacations, students are enjoying the rest of the summertime. Black Mercedes stopped near the tall skyscraper in the city centre. Dark-haired man got out of his car and looked around. The view of summer New York is wonderful. He inhaled the scent of summer and smiled slightly.

It was Damon Salvatore, 22 years old businessman who just received a big inheritance of his unknown uncle. And now Damon was going to start his own business in the company that his dad, Giuseppe Salvatore, gave him 2 months ago. Damon wasn't a really good leader because of his complex nature. He was stubborn, independent and very purposeful; no one can ever change his mind except, probably, his best friend, Alaric Saltzman, who was a co-owner of the new company. He was the only one who could stop Damon from useless and stupid deals, which Damon was making very often.

Young man locked his car and got into the high building – his new company called 'Salvatore Industries'. Damon's office was in the last floor but he usually stopped on the first floor to talk with some lovely ladies who were from his staff. Damon was handsome, so he rarely left without the company of beautiful and young women. Meanwhile, Damon finally reached his office where he unexpectedly met Alaric. His friend was waiting for Damon to come for over an hour but Damon didn't care, it was summer and he didn't want to wake up at 7AM.

- 'Seriously, Damon? Again? – Alaric's voice was irritated and his face looked really angry, - it's 10AM, Damon!'

- 'Oh, man, - Damon put his hand on Alaric's shoulder, - Chill out. It's _only_ 10AM'.

- 'Damon, you...', - Alaric was about to start abusing him but Damon quickly interrupted.

- 'Oh Rick, stop being an annoying dick. It's summer, let's get out and have fun for a while. Business can wait', - Damon's voice was calm and indifferent. And without Rick's answer Damon left the room.

- 'Caroline? Sweetie, where are you?' – Lovely voice filled the hall. Damon's voice.

- 'Mr. Salvatore, stop calling me sweetie, I don't like it.' – Girl's voice was calm but a bit disgruntled.

- 'But I like it, sweetie. - There was a smile on Damon's face and he came closer to the girl sitting at the office desk, - Better tell me, any call for me?'

- 'No, Mr. Salvatore, nothing for now.' – She said it loudly and continued assorting documents.

- 'Perfect. Then, I'm officially free for today. See you.' – With these words Damon approached the elevator and, as it arrived, left the hall.

**Hartsfield-Jackson Atlanta International Airport. Atlanta, Georgia.**

'Registration on a flight from Atlanta to New York starts in 10 minutes '. – Woman with a lovely voice from reception informed people about the flight.

Elena was running down the stairs. She was absolutely late and very nervous about it. First flight in her life must be really exciting. But also she was worried because her brother Jeremy couldn't move to NY with her. His admission to college took much longer than he expected.

Elena's bag was so heavy so she couldn't run faster. She already bumped into several people. Her clumsiness always ruins girl's life. Elena finally reached the registration desk and gave a sweet woman her documents.

- 'First flight, sweetheart? – Woman asked checking Elena's documents.

- 'Is it so obvious? – Elena's voice was muffled a little and she was straightening hair all the time.

- 'Yes, - woman smiled and gave Elena her ticket. – Here, darling, good luck'.

Elena took the ticket and slowly stepped from the desk. It's 30 minutes left. A clear thought came to Elena's mind. 'I need a coffee'. - sounded in her head. The girl put her bag over shoulder and headed for the closest Starbucks.

- 'The Cocoa Cappuccino, please' – she said loudly and gave money to the young cashier.

- 'What's your name?' – A basic question was asked.

- 'Elena, - she answered. – And can you please put cinnamon there?'

- 'Sure.' – This young man wasn't in the mood to talk. Elena got it and stopped talking. After a minute, her name was pronounced and she took her drink.

After drinking her cappuccino, Elena went to hand over her luggage and sat on her sit on the board.

- 'This is going to be amazing', - she whispered to herself and closed her eyes.

**NY.**

Damon parked his car near the Grill Bar and went in. The music was so load, so it felt uncomfortable for Damon. But he promised to come and he always kept his promises. Damon found a place to sit, less load than in the bar centre, and ordered bourbon. He was waiting for his older brother to come. Stefan was working as a FBI agent and he always saved Damon's ass in different situations. He had a lunch break and asked Damon to come and talk. After 10 minutes Damon felt a hand on his shoulder and a familiar voice right behind him.

- 'Damon, long time, no see'. – Stefan said and sat near his brother.

- 'Stefan. What's the matter?' – Damon's voice was serious and he didn't have any joy in meeting his brother today.

- 'Why the long face, brother? – Stefan tried to put a smile on Damon's face but failed. – Okay, can you give me a favor?'

- 'What is it, Stefan? I don't have time for your stupid requests.' – Damon did not find any sense in this conversation.

- 'Drive with me to the FBI centre. I need to ask you about one man who escaped from prison yesterday. I think you might know him.' – Stefan's voice became serious and he looked into his brother's eyes.

- 'Umm, okay. But if it takes long, I'll leave. I don't have time for this.' – Damon finished drinking his glass of bourbon and went out of the bar. Stefan followed him and they got into the car. FBI centre was 20 minutes away from there, so they didn't waste more time and drove.

**2 hours passed.**

Elena's flight went good and she landed in NY. She took her luggage and caught a taxi.

- 'West Street, 9A, please.' – She said loudly and closed the car door. The driver just nodded and hit the gas.

**FBI centre.**

Damon and Stefan spent 2 hours trying to find the escaped prisoner's location. It was David Fell, Damon's old mate. They were studying at the same college and then David suddenly disappeared.

- 'Stefan, I really have no idea where he can be, - Damon sighed heavily and flopped down in a chair. – He can be anywhere, not only in NY'.

- 'No, no… He must be here, not far from us. He is smart; he wouldn't book any ticket because it would make him visible for us.

- 'I'm sorry but I can't help you here, brother'. – Damon rose from his chair and moved toward the exit.

- 'Wait, Damon! – Stefan loudly shouted to him, - Father asked us to have a dinner with him tonight. Will you come?'

- 'Sure'. – Damon said without any interest and left the building. Damon haven't seen his father for almost 6 months, they weren't in good relationships anymore. Damon moved out from Stefan and their father and started living his own life.

At this moment Elena entered her new apartment and wearily flopped down on the couch.

- 'Finally, fresh life, new contacts, new job. – She sighed in tired, - New York, here I am.'

_So if you liked it, please review + follow/fave :)_

_- Elena._


	2. Chapter 2 Show me what you've got

**Chapter 2. 'Show me what you've got'**

Sweet comely girl was sitting on the balcony of her new apartment with a cup of coffee. Girl's lungs were filled with fresh air and a nice smell of freshly brewed coffee was pleasing her. Elena took her diary, which was given to her around 10 years ago by her mom as a birthday gift, and, since then, Elena has been writing in it every day.

"Dear Diary, today will be different. It has to be. I will no longer be the sad little girl who lost her parents. I will start fresh, be someone new. And no matter how hard it's going to be, I'll make it through, I have to."

She put her diary on the stool and left the balcony with no longer hot cup of coffee. After a fresh and saving shower, girl turned on her laptop and started searching for a job offers. And, after a while, she came across some good and suitable ones. She wrote down addresses, took her bag and ran out of the apartment, closing the door loudly.

It was around 10:30AM and Damon was about to get up and make a hot coffee. Cute blonde girl was lying in his bed and deeply sleeping. Damon didn't even remember where he met her and how they got home. Suddenly his house was filled with a nasty sound. Such an early phone ring could be from only one person. Alaric Saltzman. Damon joylessly took his mobile and clicked on green handset.

- "Yes."– Damon's voice was very unpleasant.

- "Do you have any idea what time it is now?!"– Alaric shouted into the phone and angrily sighed.

- "Um, around 10… probably… Why?" – Damon answered without any interest in his voice and turned on the loudspeaker.

- "10:30 to be exact. You must have been in office 2 hours ago, Damon. What the hell are you going to do when your father comes? He gave you this company not to spend your time sleeping with women every day but to be a leader."

- "Blah blah blah, how boring you are! I'll be there soon." – Damon coughed and put the phone down.

"This guy is such a boredom." – Damon thought while making himself a cup of a freshly brewed coffee. Damon wasn't in a good mood today, that's why he rudely kicked out a sweet young girl who was lying in his bed few minutes ago. He didn't come on dinner with his brother and father yesterday. It was a bad decision because his father was about to come and check how was the company doing. Damon hardly sighed, put on his jeans and shirt and went out of his house with a cup of coffee in his hand.

Elena was running like hell because she had no idea where she was at that exact moment, her geographical knowledge wasn't really good and an interview in one of the companies from her list was about to start. She panicky looked around, trying to find any familiar street but all her attempts were unsuccessful. Elena felt like she wasn't even American because all the names were so different and all people seemed very popular and famous and she didn't have any chance to become one of them. Elena pulled out a city map and tried to find her location. Girl didn't see that a road was about two steps from her and she moved ahead, still looking in the map. Black Mercedes's driver tried his best to stop until he bumped in her. But thankfully Elena looked up and saw the car moving towards her. The driver hit the brake pedal with full force. Elena made a move backwards just in time and car only touched her a little bit though it made her fall on her back. Driver got out of his car with lightning speed and bent down to Elena. The girl wasn't injured but her back hurt a little bit.

- "Are you okay?! – Damon asked loudly and helped her to sit. – Should I call an ambulance?"

- "No… no need for this… I'm… I'm fine", - Elena tried to speak load but she was still in shock and all she could do were to lean on his shoulder and to pull her gaze away from his blue eyes.

- "You sure? Let me help you, - Damon did his best not to make any sudden movements and lifted the girl to her feet, - I'm Damon..." He was weirdly polite with this girl though he's never been such a gentleman before with other women. Damon was actually shocked himself and looked a little funky.

- "Elena… Thank you, Da… Damon", – she tried her best not to shiver.

- "No need to thank me, it was my entire fault. Can I do something for you? Just ask."

- "Um… no, thank you. I'm alright." – Elena smiled slightly and put her hand off his shoulder.

- "Fine. Elena, I'm so sorry." – Damon gently removed his hand from her waist and gave her a worried look.

- "It's okay, don't be sorry, Damon."– She turned around and accidentally touched his hand by her hand but acted like she didn't notice it.

Damon was staring at her leaving and suddenly felt a hollow feeling in his chest.  
"No, man, you don't have time for this." – His thoughts brought him back to real; he got into the car and hit the gas.

It's been 30 minutes after the last event and Elena was already on her way to another organization which needed a new secretary. Gilbert was praying to get this job because she needed to pay the rent of her apartment soon or the owner would kick her out. She was running fast and after 3 minutes she reached a big building in the city centre. On the front part of the skyscraper there was written "Salvatore Industries". Elena didn't find this "Salvatore" name familiar and she thought that would be really good to work in such a nice and huge place. She sighed hardly and entered the building. Inside it looked even better than outside. Mirrors were everywhere, people had very cosy uniforms and they seemed very polite. Walls were adorned with beautiful modern pictures and graffiti. Halls were filled with many armchairs and sofas and there were TVs and computers everywhere. Everything pointed to the fact that the company was ran by a young and modern man or woman, but probably a man because of a huge number of beautiful women in staff. Elena needed to go on the last, 120th, floor, so she didn't waste much time looking around. Lifting up took her around 3 minutes but she already seemed very tired and bored, she never liked elevators. As soon as she got out of elevator, she came across a sweet young lady with blonde hair and blue eyes.

- "Hi, I'm Caroline. You came for interview?" – Her voice was so positive and smiley, so Elena suddenly felt really happy and calm. This girl was definitely on the bright side of life.

- "Yeah, I want to work as a new secretary for… – Elena started searching the name in her mobile, - Oh yeah, Mr. Salvatore. He needed a secretary who could check his business deals, as far as I know."

- "Exactly, honey. Unfortunately, he's not in the office yet, and you should know, he never comes in time, - Caroline smiled and gave a slight laugh, - But you can wait for him here," - she showed Elena a comfortable sofa and gave her some magazines to read.

After 40 minutes, Caroline received a call from Mr. Salvatore and she quickly said to Elena that he would be there in 10 minutes. Elena felt really nervous and worried. She pulled out her portfolio, gave it to Caroline and finished drinking a glass of water, which Caroline brought her a few minutes ago. Meanwhile, Black Mercedes has arrived to the building and Damon got out. He still felt a little weird because of an accident with Elena but he tried to concentrate because his father was about to come in a few minutes and Damon was sure that he would be really mad. Damon entered the building and, as usual, stopped to talk with some lovely ladies from his staff. After a while, he finally got into the elevator. Elena was sitting on the sofa when she heard a sound of opening doors. And then she saw _him._ Mr. Salvatore. _Damon_ Salvatore, to be exact. The guy who bumped into her a few minutes ago; the guy who probably was going to be her new boss. Elena couldn't breathe for some time until their eyes met. Damon's face expressed an incredible surprise. And Elena couldn't resist his ocean blue eyes; she was staring at him until Caroline broke the silence.

- "Mr. Salvatore, this is Elena Gilbert, she came to have an interview with you about a new job," – Caroline gave him Elena's portfolio and looked at Elena. She looked like she just saw a ghost; her face expressed amazement and a little bit fear and danger.

- "Elena… Gilbert? – Damon mumbled under his breath, - Sure, let's go into my office, Miss Gilbert."

Elena slowly got up from the sofa and followed him. As soon as the door was closed and they were alone, Damon promptly turned around and moved close to Elena.

- "What are you doing here?!" – His voice was strangely rude and angry and he made Elena bump into the door.

- "I just came to get a job, OK?! – she tried to move towards him but he didn't let her, - What's wrong with you?"

Damon's face suddenly became calm and regretful and he moved backwards, letting Elena move away from the door.

- "Hey, I'm sorry, I didn't mean to scare you, Elena. – His eyes were full of sorrow, - Have a seat." With these words he turned around and walked to his chair. Elena swallowed hard and moved to her chair in front of him.

- "So… you want a job here, right? As my new secretary…"- Damon was flipping through Elena's portfolio.

- "Yeah, I do."

- "Great, I like your portfolio and you have very good recommendations. You got it." – Damon looked up and gave her a big smile.

- "I'm your new secretary? Seriously? – Elena smiled back and looked into Damon's eyes. They were magnetic and irresistible. – Thank you so much, D… Mr. Salvatore. You won't regret, I promise."

- "I'm sure I won't."

They were staring at each other's eyes till Caroline walked in and broke the eye-connection.

- "Mr. Salvatore… your father is here. Should I invite him?"

Damon's mood suddenly changed, he promptly stopped this eye-connection and looked at Caroline with preoccupied look.

- "Yes, please, Caroline."

Caroline just nodded and left the office. In a minute, Giuseppe Salvatore came in. He was very well-dressed, with gray hair and the same blue eyes, which Damon had; his suit seemed really expensive. He gave his son a concentrated look and then looked at Elena. She abruptly stood up and stretched out her hand.

- "Good afternoon, Mr. Salvatore. My name is Elena Gilbert and I'm a new secretary of Da… Your son."

- "Great meeting you, Miss Gilbert, if you don't mind, I'd like to have a chat with my son one on one." – He shook her hand and gave a kind smile. Right after Elena left the office, his face absolutely changed.

- "Damon, as I can see, you don't work hard, do you?"

- "Father, take it easy. I will work, I promise. Just give me some time." – Damon tried to be "as cool as cucumber" but still, his voice trembled and he looked nervous.

- "Oh really, Damon? You didn't come yesterday, how can I trust you? – Giuseppe's voice became stronger, - I'm not going to waste time for that. I give you one week. During it you have to prove that you deserve this company or I'll take it away." – With this words Giuseppe got up from his chair and left the office, leaving Damon speechless.

Elena was sitting on the sofa and waiting for Damon to finish his chat when she heard his father's load voice and the sound of opening door. As soon as she looked up, she saw Giuseppe Salvatore coming out of Damon's office. He nodded and smiled. When he left the hall, Damon promptly got out of his office and moved towards Caroline.

- "If there are calls, write down all of the messages. And if anyone asks for me, tell I'm busy and ask to leave a message, got it?" – Damon's strong voice made Caroline a little nervous but she quickly nodded.

- "Damon! – Elena's voice interrupted him from going back to his office, - What about me?"

- "You… Um… Give Caroline your mobile number. She'll call you and tell everything you need. Good bye, Elena." – With these words he left the hall.

Elena gave her mobile number to Caroline, also Caroline gave her number, so they could be in touch, and Elena left the building.

* * *

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